2-Methylsuccinic acid

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2-Methylsuccinic acid
2-MeSuccinicAcid.png
Names
Preferred IUPAC name
Methylbutanedioic acid
Other names
Pyrotartaric acid; 2-Methylbutanedioic acid; Propane-1,2-dicarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.144 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-857-1
PubChem CID
UNII
  • InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
    Key: WXUAQHNMJWJLTG-UHFFFAOYSA-N
  • CC(CC(=O)O)C(=O)O
Properties
C5H8O4
Molar mass 132.115 g·mol−1
AppearanceWhite solid
Melting point 117.5 °C (243.5 °F; 390.6 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Methylsuccinic acid is an organic compound with the formula HO2CCH(CH3)CH2CO2H. A white solid, it is the simplest chiral dicarboxylic acid. It is a recurring component of urban aerosols. [1] Salts and esters of 2-methylsuccinic acid are called 2-methylsuccinates.

Preparation

It can be prepared by partial hydrogenation of itaconic acid over Raney nickel. [2] Alternatively, hydrocyanation of ethyl crotonate affords an intermediate, which converts to 2-methylsuccinic acid after hydrolysis of the ester and nitrile substituents. [3]

Related Research Articles

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3−x
O2−
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<span class="mw-page-title-main">Chloroalanine</span> Chemical compound

Chloroalanine (3-chloroalanine) is an unnatural amino acid with the formula ClCH2CH(NH2)CO2H. It is a white, water-soluble solid. The compound is usually derived from chlorination of serine. The compound is used in the synthesis of other amino acids by replacement of the chloride. Protected forms of the related iodoalanine are also known.

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References

  1. Kawamura, Kimitaka; Ikushima, Kouichi (1993). "Seasonal Changes in the Distribution of Dicarboxylic Acids in the Urban Atmosphere". Environmental Science and Technology. 27 (10): 2227–35. Bibcode:1993EnST...27.2227K. doi:10.1021/es00047a033.
  2. R. F. Feldkamp; B. F. Tullar (1954). "3-Methylthiophene". Org. Synth. 34: 73. doi:10.15227/orgsyn.034.0073.
  3. George Bosworth Brown (1946). "Methylsuccinic acid". Org. Synth. 26: 54. doi:10.15227/orgsyn.026.0054.